
Vacation rentals in Oconomowoc
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Top-rated vacation rentals in Oconomowoc
Guests agree: these stays are highly rated for location, cleanliness, and more.

Exhale, rest
Exhale. The perfect combination. This home is right in the village of Menomonee Falls with great shopping and restaurants within walking distance. Close to the highway, it’s also a mere half an hour to anything Milwaukee so games, museums, festivals are all also at your fingertips. At the end of dead end road with views of the river, access to trails, and a secluded deck and fire pit, there is definitely also a rural feel. This location has it all. Go out, live life, come back, exhale and rest.

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

Black Squirrel Farmhouse - (Downtown Oconomowoc)
Downtown Oconomowoc, beach, bandshell, bars, shops, restaurants, lakes, kayak/boat rental, 2 public golf courses in town and 3 more within 10 minute drive, 31 parks including the imagination station million dollar play area!!! Lots of local hiking and bike trails through the kettle moraine, visit Lapham peak, government hill, scuppernong, and much more! Minutes to Holy Hill, from the tower you can see the beautiful Lake Country area for miles. Only 1.25 hr drive to the Devils lake state park!

Cozy cottage in the heart of Lake Country
Entire cottage in the heart of Lake Country. Merryhill Cottage is nestled on two acres with mature trees. Included on the two acres- the host's farmhouse, a guest house and barn. The feeling of a country setting but with easy access to Hwys 16, 83 and I 94. Close to shopping, restaurants, parks, hiking, cross country skiing and snowshoeing, lakes, and beaches (10 min. to Delafield and Oconomowoc and 15 min. to Pewaukee.) Perfect for day trips to Madison (54 min.) and Milwaukee (30 min.).

The Loft @ The Butler Place. 1846 homestead.
The Loft at the Butler Place is a beautiful, quiet retreat set in the rural suburb of Sussex, just 30 minutes west of Milwaukee. The home is the 1846 homestead of the William Butler family, making the home older than the State of Wisconsin! The 2019 remodel of the Loft is in sophisticated farmhouse style and pays tribute to the history of the home in its furnishings, up cycled pieces, and beautiful setting. "Broken becomes blessed" both tells and compells as an invitation to all.

Garden Retreat in law Suite
Welcome to our in-law suite apartment featuring a full eat-in kitchen, living room, queen bed in large bedroom, walk in closet and full bathroom with walk-in shower. Our beautiful two acre yard has many areas to relax in, including a hammock and fire pit for the evenings. Twenty mins. to Erin Hills and Holy Hill and a half hour to most downtown Milwaukee attractions, as well as the RNC activities taking place this summer. Lots of city tips and suggestions for our guests.

Tosa Village Studio Apartment
Tosa Village Studio. (Wauwatosa is the first suburb west of Milwaukee). Walk to the Village and explore the boutique shops, restaurants and bars. Enjoy summer concerts in Hart Park. Miller Park (Milwaukee County Stadium - Home of the Brewers) only 3.5 miles away. Close to the Medical Complex, Froedert and Children's Hospitals. 6.5 miles to the Fiserv Forum (Home of the Milwaukee Bucks). Six miles to downtown Milwaukee. Enjoy Summerfest at the Lake Michigan shore.

Studio on the Prairie Fen
Kick back and relax at the Studio! The Studio is a 400 sq ft unique suite in the lower level of our home. A private locked entrance opens up to a sunny space with great views of a wetland beyond the backyard. Private patio to enjoy morning coffee and the sunrise. A great place to unwind and enjoy nature's beauty! We have binoculars if you love bird watching, and bikes to ride or hike the Glacial Drumlin Trail just 0.1 mile from the front door. Lic LICHMD-2021-00621.

1853 Farmhouse Apartment
Welcome to a two-bedroom apartment. The space includes a private bathroom, kitchen and living area. There is no kitchen/dining table. The apartment is on the second floor of the house and has an outside staircase leading up to it. The entrance/staircase is not shared by the hosts and there are no shared spaces in the home. The staircase may be steep for persons who have difficulty navigating stairs. Guests are welcome to use the patio area on the property.

Quiet Lake Country Retreat
Charming single family home located in the Village of Oconomowoc Lake. Well appointed for longs stays or perfect for a weekend retreat. Easy access to I94 and Hwy. 16. Minutes away from Olympia Resort, stores, restaurants, downtown Oconomowoc. 10 minute drive to Delafield. 20 minute drive to Erin Hills, site of the 2017 US Open. 35 minutes to downtown Milwaukee. 45 minutes to Madison. *** Coming fall 2024 the back patio will be completely renovated.

Family friendly farmstay just outside Milwaukee
The Inn at Paradise Farm is an original 1847 log homestead in rural Wisconsin just a short drive from Milwaukee and close to many attractions, especially for nature lovers. Our very spacious private 4-room suite with private entrance is comfortable for couples, families, or business travelers who long to unwind in a pastoral setting. Visit with, and even help care for, our friendly animals! We are licensed and inspected. Paradise Farm welcomes all.

Glamping Cabin on Cold SpringTree Farm
Unfortunately we can't accommodate same day bookings as we don't have enough lead time to prep the cabin for your stay. Glamping on a working Christmas tree farm. Beautiful single room stone cabin with loft and wood burning stove. Two small beds in loft and futon on main floor folds out into full bed. Lots of room around to pitch tents as well. Situated on 40 acres of land with a pond, barn with basketball court, creek and Christmas tree fields.
Popular amenities for Oconomowoc vacation rentals
Other great vacation rentals in Oconomowoc

Custom Home with Lake Views + Cozy Fireplace

Oconomowoc Downtown River View

Lake Nagawicka Escape- Dock Across the street!

Beautiful home on Okauchee Lake, WI

Pewaukee Serenity Cottage: Whimisical by the Lake

Mariner's Point Carriage House

Forest Bay Cottage

Cheerful, open space, and relaxing 1 bedroom home.
Frequently Asked Questions
Where should I stay in Oconomowoc?
Make yourself at home in Oconomowoc by choosing from our most frequently booked neighborhoods. We have over 20 vacation rentals in Wren Crest, over 20 vacation rentals in Summit, and over 20 vacation rentals in Worthingtons.
Are there vacation rentals with a dedicated workspace in Oconomowoc?
Yes! Work meets play with ease at over 10 vacation rentals in Oconomowoc featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Oconomowoc?
Experience the best of Oconomowoc with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Oconomowoc have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Oconomowoc?
Oconomowoc has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Oconomowoc have wifi?
Absolutely! We offer over 20 house rentals with wifi in Oconomowoc. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Oconomowoc
Total vacation rentals
Explore 20 vacation rentals in Oconomowoc
Nightly prices starting at
Oconomowoc vacation rentals start at $60 per night before taxes and fees
Verified guest reviews
Over 950 verified reviews to help you choose
Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 of Oconomowoc vacation rentals include wi-fi access
Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Oconomowoc rentals
4.9 Average rating
Oconomowoc stays are highly rated by guests—averaging 4.9 out of 5!
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